Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives

Autor:	S. V. Simakov, Kh. S. Shikhaliev, V. G. Kartsev, O. E. Sidorenko, A. S. Shestakov
Rok vydání:	2009
Předmět:	Indole test chemistry.chemical_compound chemistry Aryl Organic Chemistry Organic chemistry chemistry.chemical_element Cyanamide Alkylation Nitrogen Sulfur Isocyanate Methyl iodide
Zdroj:	Russian Journal of Organic Chemistry. 45:777-782
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428009050224
Popis:	Reactions of methyl 3-amino-1H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5H-pyrimido[5,4-b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1H-pyrimido[5,4-b]indol-4(5H)-ones undergoing alkylation at the sulfur atom. The reactions with benzoylcyanamide and N-(4,6-dimethylpyrimidin-2-yl)cyanamide resulted in N-(4-oxo-4,5-dihydro-3H-pyrimido-[5,4-b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3H-pyrimido[5,4-b]indol-4(5H)-ones respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::59da8422ef742a834a1171d9493b91f4 https://doi.org/10.1134/s1070428009050224 Zobrazit plný text záznamu Plný text ve formátu PDF